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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Home in Chicago
Victorian House in Heart of Rogers Park
3 bedrooms, 3 beds, 2.5 private bathrooms
26–31 Oct
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4.98 out of 5 average rating, 140 reviews
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Featured hotel
Hotel in Rosemont
Sonesta Chicago O'Hare Airport Rosemont, Accessib.
1 bedroom, 1 king bed, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest house in Chicago
Horner Park Coach House
1 bedroom, 2 beds, 1 bathroom
13–18 Dec
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed, 1 bathroom
6–11 Dec
4.97 out of 5 average rating, 635 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 double bed, 1 bathroom
5–10 Nov
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 35 reviews
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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 111 reviews
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Jan
4.95 out of 5 average rating, 135 reviews
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Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Guest house in Chicago
Cozy Coach House
1 queen bed, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 515 reviews
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Top guest favourite
Home in Chicago
2BD/1 BA with summer patio in quiet Roscoe Village
2 bedrooms, 2 beds, 1 bathroom
16–21 Nov
4.96 out of 5 average rating, 179 reviews
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Top guest favourite
Guest suite in Chicago
Gorgeous, cozy 1-bedroom Suite in Andersonville
1 bedroom, 1 queen bed, 1 bathroom
15–20 Nov
4.96 out of 5 average rating, 417 reviews
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Top guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 178 reviews
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Guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Nov
4.95 out of 5 average rating, 318 reviews
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.95 out of 5 average rating, 76 reviews
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Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds, 2 bathrooms
1–6 Nov
4.9 out of 5 average rating, 42 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Room in Chicago
Al's Oasis Chicago
1 queen bed, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 244 reviews